Tetrahedron letters

Synthesis of vinylic epoxides via arsonium ylides

JB Ousset, C Mioskowski, G Solladie

Index: Ousset, J.B.; Mioskowski, C.; Solladie, G. Tetrahedron Letters, 1983 , vol. 24, # 41 p. 4419 - 4422

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Citation Number: 29

Abstract

Recently Still 1 demonstrated the synthetic utility of nonstabilized arsonium ylides by performing a highly stereoselective synthesis of trans-epoxides. It is also known that stabilized ylides react with carbonyles to give alkenes like phosphonium ylides '. In this communication we report that allylic arsonium ylides react cleanly with aldehydes and ketones to give vinylic epoxides with the highest yields ever reported for direct epoxidation ...